5-乙酰氧基-2-甲氧基-3-甲基-环戊-2-烯-1-酮 | 102369-52-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-乙酰氧基-2-甲氧基-3-甲基-环戊-2-烯-1-酮
• 英文名称: 3-methoxy-4-methyl-2-oxocyclopent-3-enyl acetate
• 英文别名: 5-acetoxy-2-methoxy-3-methyl-cyclopent-2-en-1-one；5-acetoxy-2-methoxy-3-methyl-cyclopent-2-enone；5-Acetoxy-2-methoxy-3-methyl-cyclopent-2-enon；(3-Methoxy-4-methyl-2-oxocyclopent-3-en-1-yl) acetate
• CAS: 102369-52-8
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: GVENNTUOVOVTCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-乙酰氧基-2-甲氧基-3-甲基-环戊-2-烯-1-酮 在 phosphate buffer 、 CCL lipase 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以42%的产率得到(-)-5-hydroxy-3-methyl-2-methoxy-2-cyclopenten-1-one
  参考文献：
  名称：

  A new and efficient chemoenzymatic route to both enantiomers of α′-acetoxy and α′-hydroxy-α-methoxy cyclic enones

  摘要：

  A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy and alpha'-hydroxy-alpha-methoxy cyclic enones starting from alpha-hydroxy cyclic enones is described. Protection of 1,2-diketones, manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha'-acetoxy enones gives acetoxy enones 3a-d and hydroxy enones 4a-d with high enantiomeric excesses (up to 99%) and good yields. The transesterification of rac-4b in the presence of DMAP afforded (+)-4b and (-)-3b in high enantiomeric excesses (91-94%) and good chemical yields. (c) 2006 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.01.025
• 作为产物：
  描述：

  2-甲氧基-3-甲基环戊-2-烯-1-酮 在 manganese triacetate 作用下， 以 苯 为溶剂， 反应 34.0h， 以60%的产率得到5-乙酰氧基-2-甲氧基-3-甲基-环戊-2-烯-1-酮
  参考文献：
  名称：

  使用乙酸锰 (III) 与羧酸结合对 α-烷氧基烯酮进行 α'-氧化

  摘要：

  摘要 在各种羧酸存在下，使用乙酸锰 (III) 对 α-烷氧基-α, β-不饱和酮的环状衍生物进行 α-氧化，为合成 5-酰氧基-2-烷氧基-2-环戊烯酮和 6 -酰氧基-2-烷氧基-2-环己烯酮。

  DOI：

  10.1080/00397919308009814

文献信息

• Potassium permanganate/carboxylic acid/organic solvent: a powerful reagent for enone oxidation and aryl coupling reactions
  作者：Ayhan S. Demir、Hamide Findik

  DOI：10.1016/j.tet.2008.05.004

  日期：2008.6

  with potassium permanganate and acetic acid, in which acetoxylation products were obtained in 74–96% yields. The same reaction was carried out with carboxylic acids other than acetic acid, which furnished corresponding acyloxy ketones with the same regioselectivity. For the first time, formyloxylation products were synthesized in a 61–85% yield by using formic acid. The potassium permanganate and acetic

  用高锰酸钾和乙酸进行烯酮的α'-乙酰氧基化和芳族酮的α-乙酰氧基化，得到乙酰氧基化产物的产率为74-96％。用乙酸以外的羧酸进行相同的反应，这提供了具有相同区域选择性的相应的酰氧基酮。首次使用甲酸以61-85％的产率合成了甲酰氧基化产物。高锰酸钾和乙酸法也用于芳基偶联反应。苯中的芳基硼酸和芳基肼与高锰酸钾和乙酸的反应反过来提供了85-96％的收率。我们已经证明高锰酸钾/羧酸/有机溶剂的行为像乙酸锰（III）。
• Hesse et al., Justus Liebigs Annalen der Chemie, 1957, vol. 609, p. 57,67
  作者：Hesse et al.

  DOI：——

  日期：——
• A new and efficient chemoenzymatic route to both enantiomers of α′-acetoxy and α′-hydroxy-α-methoxy cyclic enones
  作者：Ayhan S. Demir、Zerrin Caliskan、A. Ebru Aydin、Isil Bicer

  DOI：10.1016/j.tetasy.2006.01.025

  日期：2006.3

  A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy and alpha'-hydroxy-alpha-methoxy cyclic enones starting from alpha-hydroxy cyclic enones is described. Protection of 1,2-diketones, manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha'-acetoxy enones gives acetoxy enones 3a-d and hydroxy enones 4a-d with high enantiomeric excesses (up to 99%) and good yields. The transesterification of rac-4b in the presence of DMAP afforded (+)-4b and (-)-3b in high enantiomeric excesses (91-94%) and good chemical yields. (c) 2006 Elsevier Ltd All rights reserved.
• The α'-Oxidation of α-Alkoxy Enones Using Manganese(III) Acetate in Combination with Carboxylic Acids
  作者：Ayhan S. Demir、Arman Saatcioglu

  DOI：10.1080/00397919308009814

  日期：1993.3.1

  Abstract The α-oxidation of cyclic derivatives of α-alkoxy-α, β-unsaturated ketones using manganese(III) acetate in the presence of various carboxylic acids provided a convenient synthesis of 5-acyloxy-2-alkoxy-2-cyclopentenones and 6-acyloxy-2-alkoxy-2-cyclohexenones.

  摘要 在各种羧酸存在下，使用乙酸锰 (III) 对 α-烷氧基-α, β-不饱和酮的环状衍生物进行 α-氧化，为合成 5-酰氧基-2-烷氧基-2-环戊烯酮和 6 -酰氧基-2-烷氧基-2-环己烯酮。